(S)-5-(2-amino-3-((tert-butyldimethylsilyl)oxy)propyl)-4-bromo-2-methoxy-3-methylphenol | 1448530-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-5-(2-amino-3-((tert-butyldimethylsilyl)oxy)propyl)-4-bromo-2-methoxy-3-methylphenol
• 英文别名: 5-[(2S)-2-amino-3-[tert-butyl(dimethyl)silyl]oxypropyl]-4-bromo-2-methoxy-3-methylphenol
• CAS: 1448530-84-4
• 化学式: C₁₇H₃₀BrNO₃Si
• 分子量: 404.42
• InChiKey: MZRHZJMBCJZVJD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-(2-amino-3-((tert-butyldimethylsilyl)oxy)propyl)-4-bromo-2-methoxy-3-methylphenol 在 20% palladium hydroxide-activated charcoal 、 氢气 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 2,2,2-三氟乙醇 、 丙酮 、 甲苯 为溶剂， 生成 (1S,3S)-ethyl 8-acetoxy-3-(((tert-butyldimethylsilyl)oxy)-methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009
• 作为产物：
  描述：

  在 四丁基氟化铵 、 氯化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 2.42h， 生成 (S)-5-(2-amino-3-((tert-butyldimethylsilyl)oxy)propyl)-4-bromo-2-methoxy-3-methylphenol
  参考文献：
  名称：

  Synthetic studies on lemonomycin: construction of the tetracyclic core

  摘要：

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.009

文献信息

• Synthetic studies on lemonomycin: construction of the tetracyclic core
  作者：Alberto Jiménez-Somarribas、Robert M. Williams

  DOI：10.1016/j.tet.2013.05.009

  日期：2013.9

  A substrate-induced stereocontrol strategy was used to gain access to the tetracyclic core of (-)-lemonomycin. An advanced intermediate was prepared from a known substituted tyrosinol through a 16-step sequence, which involved a Pictet-Spengler reaction, a [3+2] dipolar cycloaddition and an enamide hydrogenation. (C) 2013 Published by Elsevier Ltd.